Car of the Week: 1966 Olds 4-4-2

It might not have been the dumbest thing he’s ever done, but Paul Tyler figures it was on the short list.

For some reason — temporary insanity being the most plausible excuse — the Tampa, Fla., resident sold his beloved 1966 Oldsmobile 4-4-2. He had dreamed about owning such a car from the moment he saw a picture of one for the first time, enjoyed every minute of the 10 years he had the car, and to this day isn’t sure what possessed him to sell it to an acquaintance back in 1976.

“I don’t know why I did it. I kicked myself 1,000 times,” says Tyler, in his friendly southern drawl. “I guess I thought I needed to get it out of the garage.”

But after 10 years of regret and penance, the Car Hobby Gods apparently thought Tyler had suffered enough, and fate gave him a second chance – not just a second chance at a nice 1966 4-4-2, but a chance to buy back the same car he had once owned.

“I had not seen the fella (who bought it) in some time, and a mutual friend said to me, ‘I know you wished you hadn’t sold that car … Well, that fella is out of work and I saw him and he said he needed money. I bet you could buy it back.”

Sure enough, the car’s owner was willing to sell it back, but he too, was destined to have seller’s regret. “He said, ‘I’ll sell it to you with one stipulation: That if you ever decide to sell it again, you have to give me an option to buy it back from you!’ I told him not to worry, the car was going into my will and will be a part of my estate, and that’s the way it’s going to go. I sold it one time, and that’s all. I won’t do it again.”

“I drove out of the dealership for $2,929, sold it for $800 10 years later, then 10 years later bought it back from him, when it was 20 years old, for $4,000,” he adds with a laugh. “He had repainted it the original color while he had it, and I figured it wasn’t a bad deal because I couldn’t have had it painted and insured for $3,200. It worked out pretty good.”

Tyler’s love affair with his bronze ’66 is sort of one of those quintessential matches made in car heaven. He was smitten with the new 1966 4-4-2s immediately, ordered his car before the new models were even available, and never regretted his purchase for a minute — even 43 years later. He took delivery from Brandenburg Chevrolet in Beattyville, Kent., where he lived, in late November of 1965. The car started life as a Cutlass Holiday coupe, but the 4-4-2 package added a host of goodies that turned the car into one of the best all-around muscle cars of the era.

When it was restyled for 1966, the Oldsmobile Cutlass F-85 took on a more massive, creased-edge look. The 4-4-2 high-performance option package included seat belts, an instrument panel with a padded dashboard, a windshield washer system, two-speed windshield wipers, a left-hand manual outside rear view mirror, foam padded seat cushions, carpeting on the floor front and rear, chrome roof bow moldings, a deluxe steering wheel, front bucket or custom seats, deluxe armrests, a courtesy lamp package, 7.35 x 14 tires and seat upholstery in either all vinyl or cloth.

Under the hood of the 4-4-2 model, the 400-cid V-8 had been tweaked by another five horsepower (to 350 hp) thanks to a slight increase in compression ratio. Late in the model year, the 4-4-2 received another adrenalin injection (to 360 hp) with the one-year-only triple two-barrel carburetor setup. From the standpoints of both performance and rarity, the 1966 Olds Cutlass 4-4-2 equipped with the 360-hp factory Tri-Power installation is the most desirable example of these production years to a real muscle-car enthusiast.

Car Life magazine took one of the Tri-Power screamers from 0-to-60 mph in a mere 6.3 seconds and called it the “civilized supercar.” Quarter-mile runs were made in as little as 14.8 seconds with a terminal speed of 97 miles per hour. Car and Driver magazine test drove a 1965 Olds 4-4-2 convertible with a four-speed manual gearbox and a 3.55:1 axle in May 1965. Its 0-to-60 time was recorded as 5.5 seconds and the quarter-mile run took 15.0 seconds at 98 mph.

Tyler never tried to set any speed records in his car, using instead it as daily transportation for a decade.

“I kept the car for 10 years and sold, and 10 years later I bought it back,” Tyler said. “During that time he only put about 10,000 miles on it — something like that. When I got it back it was exactly like it was when I sold it to him, except that he had changed the (wire) wheels on it and put on some different (mag) wheels that were a factory option. When I bought it back from him, he said, ‘Your original wheels and hubcaps are in the trunk,’ so everything is pretty much original on it. The only other thing that’s been changed is the carburetor. The original carburetors had a diaphragm in them, and I had some problems with that, so I replaced the carburetor.

The engine has been rebuilt once. The car has about 117,000 miles on it, and about 11,000 since it was rebuilt.”

Tyler’s other nod to non-originality was a more mileage friendly rear end. “It came with the 390 differential, and I ran it that way for three or four years,” he recalled. “And that 390 was just eating me up with gas.”

These days, Tyler doesn’t drive his 4-4-2 as much as he used to, but he still enjoys the style, power and ride that made him choose the Olds over more popular muscle cars back in ’65. “I had friends that and Chevelle 396s, Super Sports, and had a very close friend that had a ’66 GTO, and I always felt that interior-wise, the 4-4-2 was much nicer. It just had a nicer, you might say more luxurious, look. The ride I thought was better, and I firmly believed the handling of the 4-4-2 was the best of any of them.”

“As far as I can remember, they were the only cars that had the sway bar in the rear directly from the factory …I lived up the Appalachian country in Kentucky, and drove on roads that went up and down and round and round. That handling was a big selling point to me at the time. All the automotive magazines were talking about the handling because of the sway bar in the rear.”

It’s clear from the way Tyler talks about the car that he hasn’t lost any affection for it, even though it’s no longer a daily driver and is no longer required to make tracks up and down the Kentucky high country.

“There is just something about it,” he said. “It’s become a part of the family. I’ve just always liked the design of the car and have always thought it was one of the nicest-looking cars that I had ever seen, and still have ever seen.

“Nowadays some people that look at it think. well, it doesn’t have an automatic, or doesn’t have power steering or power brakes, and of course doesn’t have air conditioning, so it has some drawbacks for Florida. But I’ve had several people try to buy it and lots of people ask for it, but I always tell them no, it’s not going to be for sale.

“I feel very lucky. I know I’m extremely lucky to have gotten it back.”

One thought on “Car of the Week: 1966 Olds 4-4-2”

I have a 1966 Cutlass Holiday Coupe (hardtop) The VIN # is 338176W308738. It has all the 442 badging and the 442 fenders. I’m trying to determine if it is a 442. I’m told that because of the loose records keeping, about the only way I’m going to determine it is a 442 is to find out what the sequential production number 308738 vehicle was when it left the factory.
Can anyone help me on this?